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Chester VT Real Estate

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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1782 Quarry Road Chester VT 05143

Chester, VT1782 Quarry Road

Price$1,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4763930

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,866

Four season retreat with VAST Trail access and great skiing close by. This 158 acre estate provides all you would want in a VT country farm/wilderness property. Sited within it's own three hilltops and at the end of a town maintained road, there is ultimate privacy. You will find open fields, wooded trails, a swimming pond and beaver ponds, a former soapstone quarry hidden within one of the peaks, a Morton Barn full of equipment and off road vehicles...even a dirt track to test your riding skills! The bldgs include a circa 1780 barn, an 1860 cape and a 1970's addition. The barn is being re-done as a grand finished space. All of the original beams are exposed. It will be a perfect studio, family room or game room upon completion. MUST be seen! The owner has also done extensive renovations to the residence to increase energy efficiency and to merge the older charm with modern improvements. The cape wing of the residence has a stunning state of the art kitchen, an open dining area, a gracious living room with re-worked original floors and a second floor master bedroom. The 1970's addition has been re-worked to enhance the bedroom spaces and the overall flow. A 2nd floor great-room boasts a massive fireplace and a great wrap-around deck to take in the beautiful views of your 158 ac acre estate. This property has been the dream project of its retired owner and this 5 year plan is coming to an end. This turnkey property awaits its next steward! Additional +/- 234 acres available.

Listed by Mark Roden of BH&G - The Masiello Group

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

40 Common Chester VT 05143

Chester, VT40 Common Street

Price$995,000The price has recently decreased

MLS Number 4730339

  • Commercial
  • Year Built 1920
  • Acreage 2.28

For over a century the Fullerton Inn has remained a keystone to historic Chester, Vermont.Though the hands of time have changed the facility and its ownership,The Fullerton has remained an institution.Having continued to deliver excellent quality of service throughout the years, since before the Civil War.The Inn has very spacious public rooms which include a huge reception room with stone fireplace and comfortable seating areas, tavern, several dining rooms, breakfast room, conference room, very large front porches and Rear deck.The front porches take in the activity of the Village plus offer alfresco dining in warmer weather.The huge rear deck allows for privacy and large parties. All 20 guest rooms have private baths and are individually decorated. There are handsome architectural features throughout the Inn.The property has been maintained and shows pride of ownership. She is an Elegant Lady.The owners quarters are a bonus. Large is an understatement. 3 bedrooms 4 baths, Living room w/Fireplace and Kitchen. Extensive upgrades to the property have taken place since the current owners purchased the Inn in 2003.They have paid particular attention to creating comfortable rooms for their guests and still offers the same warmth, comfort and professional service of 150 years ago. This is a wonderful opportunity to own a piece of Vermont History.The Inn is situated on 2.28 acres improved with the Inn, 3 or 4 bay Storage Garage, former horse barn, smaller shed & 2 Tennis Courts.

Listed by Dick Palmer of Hospitality Consultants, LLC

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$878,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4793511

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,044

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermont best ski areas which creates an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands with a sugarbush and state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

228 Vermont Route 11 Chester VT 05143

Chester, VT228 Vermont Route 11

Price$775,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4757103

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,912

Right outside the Village of Chester tucked away on a hillside, is this tastefully updated contemporary home. Terrific southern views. Totally private. With great separation of space, you will want to invite all your friends. There are four bedrooms each with their own bath including separate guest quarters with a private entrance. Delight in preparing a meal in the brand new kitchen. Dine in front of the stone fireplace. Sip a cocktail in the cozy living room. Snowshoe or mountain bike on the nearby trails. Kick your shoes off in the new slate mudroom. Relax on the outdoor patio in the summertime. So much to enjoy throughout all four seasons in Southern Vermont - close to golf and skiing at nearby Okemo Mountain Resort. This property is enrolled in Vermont's Current Use Plan to manage the forestry and generate tax benefits with additional acreage available for those who seek more land. A perfect Vermont retreat!

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2356 Lovers Lane Chester VT 05143

Chester, VT2356 Lovers Lane

Price$695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4617051

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,931

This 73.7 acre farm in Southern Vermont has been carefully managed as a family retreat providing complete privacy, and excellent views. The property includes a c1819 Farmhouse with 4,930 square feet and 6 bedrooms surrounded by stonewalls and beautiful birch trees, a 2-bedroom house, and two antique barns. The diverse landscape includes open meadows suitable for agriculture, a 2-acre pond, orchard and streams. Located just 4 hours from NYC, and 2.5 hours from Boston.

Listed by T Story Jenks of LandVest, Inc/Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1502 Popple Dungeon Road Chester VT 05143

Chester, VT1502 Popple Dungeon Road

Price$640,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4762267

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,445

Come fall in love! Just 3.5 miles from the green in Chester, is this stunning farmhouse built in 1989. A superb country location. The land is split onto both sides of the road providing permanent protection. Across the road from the house is a large, flat field that is perfect for horses and over 1,300 feet of river frontage. On the house side of the road, you will find multiple outbuildings & barns. Gardens, sheds, & a car barn with a huge studio above awaits craftspeople, writers, or exercise enthusiasts. Saving the best for last, the home is stunning. Covered porches for quiet time. Enter into a large foyer & hall. To the left is a formal parlor, & to the right, a large country kitchen with sitting room. The kitchen is every chef's dream from the appliances to the tile work. The dining room has a wall of windows overlooking the gardens & pasture. A mudroom & first-floor bedroom with bath & walk-in closet round out the first floor. Upstairs are three generous bedrooms & two baths. The home's custom features are fantastic -- tile work, painting, trim detail & more. The full, dry basement has loads of space. There is fiber optic internet, a generator, wood boiler, along with a traditional multi-zone oil boiler. This is a spot to call home for horse people, home business owners, artisans, families or retirees. Wait until you see it for yourself! Showings shall begin as soon as the Stay Home-Stay Safe Order is lifted. Let us know if you wish to be notified when that occurs.

Listed by Betty McEnaney of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

101 Stonehedge Lane Chester VT 05143

Chester, VT101 Stonehedge Lane

Price$475,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4748048

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,516

Beautiful country estate in village setting. Welcome to 101 Stonehedge - located just above the historic Stone Village in the quaint town of Chester. You will be met with a beautiful stone walled entrance and a hedge lined drive. An oversized 3 car garage has plenty of room for your vehicles as well as room to expand above. The atrium welcomes you into the home that is bright with sun filled rooms and quality finishes throughout. The 2 story living room has a fireplace, discreet wet bar, and 2 sets of French doors that lead out to a large deck. A second living space and game room provides ample room for entertaining year-round. The first floor master bedroom wing also has French doors to the deck, a den, walk in closet, and well appointed bathroom. Views of Flamstead Mountain can be seen from most rooms, the deck, and the well designed, easy care, perennial gardens. Nice sprawling grounds with ornamental trees, an arbor, brick pathways and even a chicken coop make this a perfect private retreat. Being centrally located allows ease of access to several ski areas, lakes, hiking, biking, and shopping. Come see what this home has to offer.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

244 Main Chester VT 05143

Chester, VT244 Main Street

Price$470,000The price has recently decreased

MLS Number 4720476

  • Commercial
  • Year Built 1825
  • Acreage 0.6

Built in Circa 1820 Victorian Inn is rich with history and located in the heart of Chester Village. Property offers an operating Inn with a gift shoppe, a beautiful Carriage House, flower gardens, chicken coop and peaceful lawn area separating a private cottage at the rear of the property. The Inn has beautiful details and many of its original features . Exquisite woodwork and large windows that allow for natural light. Offering six en-suite bedrooms and a small apartment space just above the gift shoppe. The common spaces include a dining area with a bay window, a cozy den with a gas fireplace and a gracious living room. The detached two-story Carriage House once offered home for horses and has a garage space for one vehicle. Both the Inn and Carriage House are registered on the National Historic Registry. The three bedroom cottage is full of character and offers privacy. Perfect for an owner, inn keeper quarters or an additional rental property. This property is a true gem with so many possibilities

Listed by Jessica Citera of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

244 Main Street Chester VT 05143

Chester, VT244 Main Street

Price$470,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4721840

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 4,424

Built in Circa 1820 Victorian Inn is rich with history and located in the heart of Chester Village. Property offers an operating Inn with a gift shoppe, a beautiful Carriage House, flower gardens, chicken coop and peaceful lawn area separating a private cottage at the rear of the property. The Inn has beautiful details and many of its original features . Exquisite woodwork and large windows that allow for natural light. Offering six en-suite bedrooms and a small apartment space just above the gift shoppe. The common spaces include a dining area with a bay window, a cozy den with a gas fireplace and a gracious living room. The detached two-story Carriage House once offered home for horses and has a garage space for one vehicle. Both the Inn and Carriage House are registered on the National Historic Registry. The three bedroom cottage is full of character and offers privacy. Perfect for an owner, inn keeper quarters or an additional rental property. This property is a true gem with so many possibilities.

Listed by Jessica Citera of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

352 Davidson Hill Road Chester VT 05143

Chester, VT352 Davidson Hill Road

Price$425,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4762698

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4,234

If you're looking for a beautiful home with lots of room, long range views from a wrap around porch with expansive deck, granite counter-tops, and room to expand...then look no further. This home boasts over 4200 square feet of living space and a separate 30' x 40' heated workshop/studio with its own bath and laundry hook ups. High ceiling basement in main house with walk out slider adds to the expansion possibilities. A radiant heating system with Munchkin high efficiency boiler coupled with a whole house Lifebreath air handler and insulated concrete foundation makes this an efficient and cost effective home to maintain. Hardwood and tile floors in the common areas adds to the beauty of this spacious home. Enjoy the huge game room that currently houses a pool table, foosball table, and ping pong table. Owner recently replace the roof, sheet rocked the garage, resurfaced driveway, and painted the deck and porch. This home is ready for the next owner to enjoy for years to come.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

665 10 Route Chester VT 05143

Chester, VT665 10 Route

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4776152

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 5,482

Are you ready to live the ultimate dream of running your own business in Vermont? Once featured in Country Inns of New England this property could be yours! Current owner once operated a successful 24 seat restaurant that includes commercial kitchen, 6 nicely appointed rooms for guests (plus two additional rooms) and owner's quarters. What do you want to do? inn, bed and breakfast, retreat, events...you name it! Located conveniently to I91, Okemo Mountain (only a few minutes drive), several other ski resorts, the shopping in Manchester and villages of Chester, Weston and Cavendish you could not ask for a better spot to live and work in Southern Vermont. There is much to love about this antique farmhouse from the ornate woodwork to the hardwood floors this property feels like home. The barn offers a multitude of possibilities (woodworking shop, dance space, yoga space, events). The outdoor space speaks to country living with gardens, pond and level yard.

Listed by Lisa Kelley and Tyleen Murray of Kelley Real Estate, Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

710 Baileys Mill Road Chester VT 05143

Chester, VT710 Baileys Mill Road

Price$365,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4790047

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,071

Privately sited among trees and open fields on 43.7 acres, this 2001 cape style home abuts 1,000's of acres of forest. The house features two bedrooms (town records say 3 bedrooms), 2 baths, a fireplace, farmers porch overlooking the field, and an open deck off the back of the house. There is a two-car attached garage. The driveway runs along a 3-acre field to a second field where the house is located. Much of the property is forested with sugar maple, red oak, white pine and hemlock.

Listed by T Story Jenks of LandVest, Inc/Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.33% last updated on 2020-04-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated April 6, 2020.

 

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